Dichloromethane → HCID 71257880, compound

Participants

Reaction Steps

In a 250 mL round-bottomed flask, 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-5-(5-(morpholine-4-carbonyl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)nicotinaldehyde (50 mg, 78.4 μmol, Eq: 1.00) was combined with dichloromethane (6 ml) and 2 mL MeOH to give a yellow solution. Sodium borohydride (3.56 mg, 94.1 μmol, Eq: 1.2) was added. The colorless solution was stirred at ambient temperature for 1 h. 1 mL of saturated NH4Cl was added; followed by 5 mL H2O. Mixture was stirred for 5 min. The reaction mixture was poured into 50 mL H2O and extracted with EtOAc (3×50 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 24 g, 1% to 3% MeOH in DCM) to afford the desired product (41 mg) as an off-white powder. (M+H)+=640 m/e. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9 H) 3.50-3.85 (s and overlapping m, 11 H) 4.51 (br. s., 2 H) 6.90 (d, J=8.59 Hz, 1 H) 7.51-7.63 (m, 3 H) 7.71 (dd, J=8.59, 2.53 Hz, 1 H) 7.79 (d, J=2.53 Hz, 1 H) 8.26 (br. s., 1 H) 8.37 (d, J=1.52 Hz, 2 H) 8.70 (d, J=5.05 Hz, 1 H) 8.82 (d, J=2.02 Hz, 1 H).

Provenance & Evidence